Hydrocarbon compound with ≥3 consecutive double bonds
Not to be confused with cumene.
Butatriene, the simplest cumulene
A cumulene is a compound having three or more cumulative (consecutive) double bonds.[1] They are analogous to allenes, only having a more extensive chain. The simplest molecule in this class is butatriene (H2C=C=C=CH2), which is also called simply cumulene. Unlike most alkanes and alkenes, cumulenes tend to be rigid, comparable to polyynes. Cumulene carbenes H2Cn for n from 3 to 6 have been observed in interstellar molecular clouds[2][3] and in laboratory experiments[4] by using microwave and infrared spectroscopy. (The more stable cumulenes H2CnH2 are difficult to detect optically because they lack an electric dipole moment.) Cumulenes containing heteroatoms are called heterocumulenes;[5] an example is carbon suboxide.
^IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "cumulenes". doi:10.1351/goldbook.C01440
^Thaddeus, P.; Gottlieb, C.A.; Mollaaghababa, R.; Vrtilek, J.M. (1993). "Free carbenes in the interstellar gas". J. Chem. Soc., Faraday Trans. 89 (13): 2125. doi:10.1039/ft9938902125. ISSN 0956-5000.
^Cabezas, C.; Tercero, B.; Agúndez, M.; et al. (2021). "Cumulene carbenes in TMC-1: Astronomical discovery of I\-H2C5". Astronomy & Astrophysics. 650: L9. doi:10.1051/0004-6361/202141274. ISSN 0004-6361. PMC 7611420.
^McCarthy, M. C.; Travers, M. J.; Kovács, A.; et al. (1997). "Detection and Characterization of the Cumulene Carbenes H2C5 and H2C6". Science. 275 (5299): 518–520. doi:10.1126/science.275.5299.518. ISSN 0036-8075.
^IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "heterocumulenes". doi:10.1351/goldbook.H02797
is also called simply cumulene. Unlike most alkanes and alkenes, cumulenes tend to be rigid, comparable to polyynes. Cumulene carbenes H2Cn for n from...
it is not encountered in everyday life. It is classified as a carbene, cumulene and an oxocarbon. Dicarbon monoxide is a product of the photolysis of carbon...
many complex molecules, such as cyanopolyynes HCnN for n = 3,5,7,9, and cumulene carbenes H2Cn for n = 3–6. The Taurus molecular cloud was identified in...
candidate for a spectroscopically observed tricarbon species. It is a cyclic cumulene. Rogers, Donald W.; McLafferty, Frank (1995). "G2 Ab Initio Calculations...
success as of 2011[update]. Calculations suggest that the alternative cyclic cumulene structure, called cyclohexahexaene, is the potential energy minimum of...
methyl groups are often explicitly written out as Me or CH3, while (hetero)cumulene carbons are frequently represented by a heavy center dot. Hydrogen atoms...
C3O2 and structure O=C=C=C=O. Its four cumulative double bonds make it a cumulene. It is one of the stable members of the series of linear oxocarbons O=Cn=O...
Ultimately, one of the triple bonds of the enediyne is converted to a cumulene. The cumulene and the remaining alkyne donate one electron each to form a new...
bonds, compounds with three or more cumulated double bonds are called cumulenes. For many years, allenes were viewed as curiosities but thought to be...
of carbon. Possible bonding patterns include all double bonds (a cyclic cumulene) or alternating single bonds and triple bonds (a cyclic polyyne). As of...
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